@article{SchmidtElizarov2012, author = {Schmidt, Bernd and Elizarov, Nelli}, title = {Selective arene functionalization through sequential oxidative and non-oxidative Heck reactions}, series = {Chemical communications}, volume = {48}, journal = {Chemical communications}, number = {36}, publisher = {Royal Society of Chemistry}, address = {Cambridge}, issn = {1359-7345}, doi = {10.1039/c2cc30752a}, pages = {4350 -- 4352}, year = {2012}, abstract = {A sequence of acetamide directed oxidative Heck reaction and deacetylation-diazotation-Heck coupling allows the traceless removal of the acetamide group and its dual exploitation as a catalyst directing group and a leaving group.}, language = {en} } @misc{SchmidtElizarovBergeretal.2013, author = {Schmidt, Bernd and Elizarov, Nelli and Berger, Ren{\´e} and H{\"o}lter, Frank}, title = {Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes}, url = {http://nbn-resolving.de/urn:nbn:de:kobv:517-opus4-95070}, pages = {3674 -- 3691}, year = {2013}, abstract = {4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4'-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior.}, language = {en} } @article{SchmidtElizarovBergeretal.2014, author = {Schmidt, Bernd and Elizarov, Nelli and Berger, Ren{\´e} and H{\"o}lter, Frank}, title = {Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes: a protecting-group economic synthesis of phenolic stilbenes}, issn = {1477-0520}, doi = {10.1039/C3OB40420J}, year = {2014}, abstract = {4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4{\"i}-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior.}, language = {en} } @article{SchmidtElizarovBergeretal.2013, author = {Schmidt, Bernd and Elizarov, Nelli and Berger, Ren{\´e} and Hoelter, Frank}, title = {Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes a protecting-group economic synthesis of phenolic stilbenes}, series = {Organic \& biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry}, volume = {11}, journal = {Organic \& biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry}, number = {22}, publisher = {Royal Society of Chemistry}, address = {Cambridge}, issn = {1477-0520}, doi = {10.1039/c3ob40420j}, pages = {3674 -- 3691}, year = {2013}, abstract = {4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4'-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior.}, language = {en} } @article{SchmidtElizarovBergeretal.2013, author = {Schmidt, Bernd and Elizarov, Nelli and Berger, Ren{\´e} and Petersen, Monib H.}, title = {From paracetamol to rolipram and derivatives - application of deacetylation-diazotation sequences and palladium-catalyzed matsuda-heck reaction}, series = {Synthesis}, volume = {45}, journal = {Synthesis}, number = {9}, publisher = {Thieme}, address = {Stuttgart}, issn = {0039-7881}, doi = {10.1055/s-0032-1316874}, pages = {1174 -- 1180}, year = {2013}, abstract = {A six-step synthesis of the antidepressant rolipram from the popular analgetic 4-acetamidophenol (paracetamol) is described. The steps include oxidative functionalization of the aromatic core, diazonium salt formation via deacetylation-diazotation, Matsuda-Heck reaction, conjugate addition of nitromethane, and hydrogenative cyclization.}, language = {en} } @article{SchmidtElizarovSchildeetal.2015, author = {Schmidt, Bernd and Elizarov, Nelli and Schilde, Uwe and Kelling, Alexandra}, title = {Dual Role of Acetanilides: Traceless Removal of a Directing Group through Deacetylation/Diazotation and Palladium-Catalyzed C-C-Coupling Reactions}, series = {The journal of organic chemistry}, volume = {80}, journal = {The journal of organic chemistry}, number = {9}, publisher = {American Chemical Society}, address = {Washington}, issn = {0022-3263}, doi = {10.1021/acs.joc.5b00272}, pages = {4223 -- 4234}, year = {2015}, abstract = {The acetamide group enables regioselective oxidative ortho-C-H activation reactions, such as Pd-catalyzed acylation. The synthetic utility of these transformations can be significantly enhanced by using the acetamide as a quasi-leaving group in a subsequent conventional Pd-catalyzed coupling or cross-coupling reaction. The concept is illustrated herein for the synthesis of o-alkenyl- and o-arylphenones, which have potential for the synthesis of arylated aromatic heterocycles.}, language = {en} } @article{SchmidtElizarovRiemeretal.2015, author = {Schmidt, Bernd and Elizarov, Nelli and Riemer, Nastja and H{\"o}lter, Frank}, title = {Acetamidoarenediazonium Salts: Opportunities for Multiple Arene Functionalization}, series = {European journal of organic chemistry}, journal = {European journal of organic chemistry}, number = {26}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1434-193X}, doi = {10.1002/ejoc.201500795}, pages = {5826 -- 5841}, year = {2015}, abstract = {Unlike their ortho counterparts, meta- and para-acetamidoanilines can be converted into the corresponding acetamidoarenediazonium salts. These offer various opportunities for multiple Pd-catalyzed arene functionalization reactions, such as Matsuda-Heck-, Suzuki-Miyaura- or Fujiwara-Moritani couplings.}, language = {en} }